DBX DROPBOX, INC.

BEARISH Impact: 5/10 Insider Cluster (6 insiders)
Horizon weeks Filed May 20, 2026 Processed 23d 17h ago
Insider cluster: 6 insiders, $1.5M total
Latest settled — T+5d ⚠ clustered
DBX ▼ -1.10% at T+5d
SHORT call ✓ call won +1.10% · α vs SPY +2.95% · entry $27.16 → $26.86
Next anchor: T+20d in 5d
Currently $27.09 · +0.25% from $27.16 entry (call sign-flipped)
Entry anchored
May 20, 2026
via day open
T+1d
+1.29%
call -1.29% · α -0.84%
$27.51
settled 23d ago
T+5d
-1.10%
call +1.10% · α +2.95%
$26.86
settled 16d ago
T+20d
call — · α —
in 5d
T+60d
call — · α —
in 2mo

Price Chart

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Executive Summary

Six insiders at Dropbox (including CEO Andrew Houston) sold a total of ~$1.45M in shares within a 5-day window, mostly at $25.96-$27.28. The CEO's $974K sale came after converting derivative shares at $0 cost basis. Tax-withholding surrenders (A/F) on 5/15 for CTO, CLO, CAO, and two other executives added $1.92M in non-cash dispositions but do not carry signaling weight. The cluster follows a Q1 earnings report where revenue grew only 0.8% YoY, GAAP net income fell 24%, and paying users contracted — suggesting insiders may be taking chips off the table after a period of heavy share repurchases ($366.8M) that inflated EPS.

Key Financial Metrics

Direction
selling
Total Value
$1.4M
Insiders
6

Actionable Insight

Despite the low proportional value (0.02% of market cap), the CEO's sale immediately after derivative conversion is a notable negative signal given Q1's contracting user base and flat revenue. The broad C-suite/director selling across 5 days adds weight. Watch for post-earnings drift and any guidance revision next quarter — revenue growth stagnation combined with insider selling is a caution flag for the stock.

Key Facts

  • CEO Andrew Houston sold 37,498 shares for ~$974K on 5/14 after converting derivatives at zero cost
  • Total open-market sales: ~$1.45M across 6 insiders (CEO, CLO, CTO, 3 directors)
  • Tax-withholding surrenders on 5/15 totaled ~$1.92M across 5 executives (non-cash, $0 to the insider)
  • Open-market sales represent ~0.02% of DBX's $6.4B market cap — below the 0.1% triviality threshold
  • Q1 2026 revenue grew just 0.8% YoY to $629.5M; GAAP net income fell 24%; paying users declined to 18.09M

Financial Impact

Open-market sales of ~$1.45M — less than 0.1% of market cap; non-cash tax withholding shuffles of $1.92M add no economic selling pressure

institutional confidenceinsider sentimentshare count

Risk Factors

  • Revenue growth stagnation (0.8% YoY) combined with user declines signals maturation of the core file-syncing business
  • CEO selling after holding period could be liquidity-driven, but timing right after earnings is unfavorable optics
  • Heavy buyback program ($366.8M in Q1) is propping up EPS but adding leverage; sustainability questioned if cash flow falters

Market Snapshot

Exchange
Nasdaq
Sector
Services-Prepackaged Software
Analyst Consensus
6% bullish (16 analysts)

Documents Analyzed

This report is based on 1 SEC document filed with EDGAR.

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-DBX-1779309069679
17 reports for DBX
Performance horizon

Track record builds as more directional reports settle.

Filters
Rows
Reports for DBX — sortable, filterable
Type Now
Jun 3, 2026
9d ago
Insider Cluster
NEUTRAL ★ 3/10
$27.18 $27.38▲ +0.75%▲ +3.35%$27.09 (−0.31%)
Jun 1, 2026
12d ago
8-K
NEUTRAL ★ 4/10
$28.92 $28.16▼ −2.63%▼ −2.77%$27.09 (−6.32%)
May 26, 2026
18d ago
8-K
NEUTRAL ★ 4/10
$26.46 $25.97▼ −1.85%▼ −1.87%$27.09 (+2.38%)
May 20, 2026
23d ago
Insider Cluster
NEUTRAL ★ 3/10
$27.16 $27.51▲ +1.29%▲ +0.84%$27.09 (−0.25%)
May 20, 2026
23d ago
Insider Cluster
NEUTRAL ★ 2/10
$27.16 $27.51▲ +1.29%▲ +0.84%$27.09 (−0.25%)
May 20, 2026
23d ago
Insider Cluster
NEUTRAL ★ 2/10
$25.97 $26.19▲ +0.84%▲ +0.29%$27.09 (+4.32%)
May 20, 2026
23d ago
Insider Cluster
BEARISH ★ 4/10
$27.16 $27.51▼ −1.29%▼ −0.84%$27.09 (+0.25%)
May 20, 2026
23d ago
Insider Cluster
BEARISH ★ 5/10
$27.16 $27.51▼ −1.29%▼ −0.84%$27.09 (+0.25%)
May 19, 2026
24d ago
Insider Cluster
NEUTRAL ★ 4/10
$27.53 $27.16▼ −1.34%▼ −1.54%$27.09 (−1.59%)
May 19, 2026
24d ago
Insider Cluster
BEARISH ★ 5/10
$27.53 $27.16▲ +1.34%▲ +1.54%$27.09 (+1.59%)
Showing 10 of 17

US Market Status

Market Closed — Opens Mon (47h 22m)

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